(3S,4R)-1-benzyl-4-(4-fluorophenyl)pyrrolidine-3-carboxylic acid

Base Information

• Chemical Name: (3S,4R)-1-benzyl-4-(4-fluorophenyl)pyrrolidine-3-carboxylic acid
• CAS No.: 80909-49-5
• Molecular Formula: C₁₈H₁₈FNO₂
• Molecular Weight: 299.345
• DSSTox Substance ID: DTXSID40513048
• Mol file: 80909-49-5.mol

Synonyms:80909-49-5;(3S,4R)-1-benzyl-4-(4-fluorophenyl)pyrrolidine-3-carboxylic acid;Trans-1-benzyl-4-(4-fluorophenyl)pyrrolidine-3-carboxylic acid;(3S,4R)-1-Benzyl-4-(4-fluorophenyl)-pyrrolidine-3-carboxylic acid;rel-(3S,4R)-1-Benzyl-4-(4-fluorophenyl)pyrrolidine-3-carboxylic acid;1821769-75-8;C18H18FNO2;TRANS (+/-) 1-BENZYL-4-(4-FLUOROPHENYL)PYRROLIDINE-3-CARBOXYLIC ACID;DTXSID40513048;Trans-1-benzyl-4-(3-fluorophenyl)pyrrolidine-3-carboxylic acid;MFCD09910402;AKOS015856063;AM20041196;A15820

Chemical Property of (3S,4R)-1-benzyl-4-(4-fluorophenyl)pyrrolidine-3-carboxylic acid

Chemical Property:

• PSA: 40.54000
• LogP: 3.06380
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 299.13215698
• Heavy Atom Count: 22
• Complexity: 375

Purity/Quality:

97% ^*data from raw suppliers

(3S,4R)-1-Benzyl-4-(4-fluorophenyl)-pyrrolidine-3-carboxylic acid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(CN1CC2=CC=CC=C2)C(=O)O)C3=CC=C(C=C3)F
• Isomeric SMILES: C1[C@H]([C@@H](CN1CC2=CC=CC=C2)C(=O)O)C3=CC=C(C=C3)F

Technology Process of (3S,4R)-1-benzyl-4-(4-fluorophenyl)pyrrolidine-3-carboxylic acid

There total 8 articles about (3S,4R)-1-benzyl-4-(4-fluorophenyl)pyrrolidine-3-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

(3R,4S)-ethyl 1-benzyl-4-(4-fluorophenyl)pyrrolidine-3-carboxylate → trans-1-benzyl-4-(p-fluorophenyl)pyrrolidine-3-carboxylic acid (1394827-82-7,80909-49-5)

Guidance literature:

With barium dihydroxide; In ethanol; for 15h; Heating;

DOI:10.1002/hlca.19810640727

Reference yield:

3-(benzylamino)propionitrile (706-03-6) → trans-1-benzyl-4-(p-fluorophenyl)pyrrolidine-3-carboxylic acid (1394827-82-7,80909-49-5)

Guidance literature:

Multi-step reaction with 6 steps

1: (i-Pr)2NEt / acetone / Ambient temperature

2: 87 percent / NaBH₄ / methanol / Ambient temperature

3: 86 percent / SOCl₂ / CHCl₃ / 2.5 h / Heating

4: 78 percent / NaN(TMS)2 / benzene; tetrahydrofuran / 1 h / 20 °C

5: 1.) HCl; 2.) HCl, H₂O / 1.) 15 h, reflux; 2.) 3 h, reflux

6: 72 percent / aq. Ba(OH)2 / ethanol / 15 h / Heating

With hydrogenchloride; barium dihydroxide; sodium tetrahydroborate; thionyl chloride; water; sodium hexamethyldisilazane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; chloroform; acetone; benzene;

DOI:10.1002/hlca.19810640727

Reference yield:

2-bromo-4'-fluoroacetophenone (403-29-2) → trans-1-benzyl-4-(p-fluorophenyl)pyrrolidine-3-carboxylic acid (1394827-82-7,80909-49-5)

Guidance literature:

Multi-step reaction with 6 steps

1: (i-Pr)2NEt / acetone / Ambient temperature

2: 87 percent / NaBH₄ / methanol / Ambient temperature

3: 86 percent / SOCl₂ / CHCl₃ / 2.5 h / Heating

4: 78 percent / NaN(TMS)2 / benzene; tetrahydrofuran / 1 h / 20 °C

5: 1.) HCl; 2.) HCl, H₂O / 1.) 15 h, reflux; 2.) 3 h, reflux

6: 72 percent / aq. Ba(OH)2 / ethanol / 15 h / Heating

With hydrogenchloride; barium dihydroxide; sodium tetrahydroborate; thionyl chloride; water; sodium hexamethyldisilazane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; chloroform; acetone; benzene;

DOI:10.1002/hlca.19810640727

upstream raw materials:

3-(benzylamino)propionitrile

2-bromo-4'-fluoroacetophenone

3-{Benzyl-[2-(4-fluoro-phenyl)-2-oxo-ethyl]-amino}-propionitrile

3-propionitrile

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